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This paper explores how the extension of contemplative qualities to intimate relationships can transform human sexual/emotional responses and relationship choices. The paper reviews contemporary findings from the field of evolutionary psychology on the twin origins of jealousy and monogamy, argues for the possibility to transform jealousy into sympathetic joy (or compersion), addresses the common objections against polyamory (or nonmonogamy), and challenges the culturally prevalent belief that the only spiritually correct sexual options are either celibacy or (lifelong or serial) monogamy. To conclude, it is suggested that the cultivation of sympathetic joy in intimate bonds can pave the way to overcome the problematic dichotomy between monogamy and polyamory, grounding individuals in a radical openness to the dynamic unfolding of life that eludes any fixed relational identity or structure.